March 18, 2025

The Progress Report

“What if this fails?” 

👆The question that keeps you up at 3 AM, staring at the ceiling. Persistent, annoying… and extremely valuable.

Today, I’m diving into how one founder turned his gut-wrenching uncertainty into a $1M monthly revenue business. Not by conquering fear, but by learning to listen to what it was telling him. 

In this newsletter:

• How Joel Gascoigne leveraged his fear to validate his venture

• Step-by-step framework to help you do the same

• A 7-day challenge to test one idea that scares you

• Putting my money where my mouth is 🫣

In partnership with

Learn AI in 5 minutes a day

This is the easiest way for a busy person wanting to learn AI in as little time as possible:

1. Sign up for The Rundown AI newsletter

2. They send you 5-minute email updates on the latest AI news and how to use it

3. You learn how to become 2x more productive by leveraging AI

Sign up to start learning.

Weekly Insight

When Joel Gascoigne came up with the idea for Buffer (a social media scheduling tool), he faced the classic founder fear: “What if I build this and nobody wants it?”

So, he met that fear head-on. Before spending months building a prototype, Gascoigne sought immediate market feedback.

He created a simple landing page describing Buffer's concept with a sign-up button–even though the product didn't exist yet.

Visitors who clicked “Sign me up” saw: “Thanks for your interest, we're not ready yet – leave your email for early access.”

(If you’re like me, you hate the idea of this approach. It feels like tricking people: promising something you can’t deliver on yet. But, realistically, no one cares. No one judges you as harshly as you do.)

Taking this approach allowed Gascoigne to measure real demand without building anything. Hitting “publish” was scary, sure, but he (correctly) weighed the risk of not knowing as worse than that of an imperfect launch.

After a month of sharing the page within his network and on Hacker News, 120 people had signed up–clear validation that his idea solved a real problem.

Encouraged by this, Gascoigne built a minimal product and started charging early customers. Within nine months, Buffer had over 100,000 users.

His approach transformed vague fears into concrete data. Buffer grew into a business with over $1 million in monthly revenue because Gascoigne wasn't paralyzed by what could go wrong.

The real fix for fear isn't courage or confidence—it's getting curious and taking action while everyone else is still overthinking.

Intent to Action

Follow Buffer's playbook and face your fears, head-on.

1. Identify what scares you most 

Is it that no one will use your product? That your pricing is wrong? That a new feature won't resonate? Name the specific fear that's holding you back.

2. Design the simplest possible test 

Create a minimal experiment that tests just this assumption—nothing more:

• For a new product: Use Leadpages or Unbounce to build a landing page with a simple product overview and a sign-up button

• For a new feature: Create a new page for the feature on your site, label it descriptively, add a product overview to the page and track clicks to it

• For services: Offer pre-sales at a discount before building out the complete offering

3. Define your “go/no-go” signal 

Before you start, decide what success looks like:

• 50 email sign-ups in two weeks?

• 10% of visitors clicking your “pre-order” button?

• 5 people willing to get on a call to learn more?

4. Share strategically 

“Build it and they will come” is, frankly, bad advice. Accept that, then come up with a plan. Share your experiment where your potential customers already gather—specific subreddits, Facebook groups, or industry forums.

Resist the urge to neutralize your messaging by calling it market feedback or product testing. Market the test as you would market a live product.

5. Act on what you learn 

Remember that your real goal here is to gather information:

• If signals are positive: Build the simplest version that delivers value, then test it

• If signals are mixed: Refine your positioning and test again

• If signals are negative: Thank the universe for saving you months of wasted effort

Closing Thought

Fear of failure isn't something you conquer. You have to learn to accept it, then turn it into your advantage.

Build constrained, strategic experiments to transform vague fears into clear data points and next steps. You'll still feel the fear—but you'll see it as a signal you're pushing boundaries, not a warning to retreat.

Next week, I’ll explore how you can build a community to help validate ideas, avoid common mistakes and—perhaps most importantly—feel less alone in your journey.

See you then.

Your Weekly Challenge

Identify one fear that's holding your business back, then design a simple 7-day experiment to test it.

Hit reply and tell me what you hope to learn—if you’re not sure how to test it, I’ll help you come up with ideas. If you already know how you’ll test it, I’ll hold you accountable.

Money Where My Mouth Is

Speaking of facing fears… I'm doing something that makes me uncomfortable: stepping out from behind the “Digital Entrepreneur” brand to write to you directly.

Hi, I'm Simon. 

I've been the voice behind these newsletters all along, but today I'm taking my own advice and stepping out into the light. Why? Because I believe connecting person-to-person is more valuable than speaking as a faceless brand.

Is this the right move? Like Gascoigne, I won't know until I try. So consider this my own fear-testing experiment. 

If you appreciate this more personal approach (or if you prefer the previous style), hit reply and let me know. Your feedback will determine whether this becomes our new normal.

This feels vulnerable. And that's probably a good sign. 🤷🏻‍♂️